Lac-Phe

Lactoylphenylalanine, or Lac-Phe, is an N-lactoyl-amino acid metabolite produced by mammals and microorganisms.^{[1][2][3][4][5]} In humans, levels are increased by intense exercise and in the inborn error of metabolism phenylketonuria.^{[6][7][8][1][9]} In mice, high levels of Lac-Phe in the blood cause a decrease of food intake^[6] and in humans, its production has been shown to correlate with adipose tissue loss during an endurance exercise intervention.^[10] In mammals it is created from (S)-lactate and L-phenylalanine by the cytosol nonspecific dipeptidase (CNDP2) protein.^[1] It is classified as N-acyl-alpha-amino acid and pseudodipeptide.^[11]

Lac-Phe

Names
IUPAC name (2S)-2-[[(2S)-2-hydroxypropanoyl]amino]-3-phenylpropanoic acid
Other names N-[(S)-lactoyl]-L-phenylalaninate N-Lactoyl-phenylalanine N-Lactoylphenylalanine
Identifiers
CAS Number	183241-73-8
3D model (JSmol)	Interactive image
ChEBI	CHEBI:174217
ChemSpider	9250603
PubChem CID	11075454
InChI InChI=1S/C12H15NO4/c1-8(14)11(15)13-10(12(16)17)7-9-5-3-2-4-6-9/h2-6,8,10,14H,7H2,1H3,(H,13,15)(H,16,17)/t8-,10-/m0/s1 Key: IIRJJZHHNGABMQ-WPRPVWTQSA-N
SMILES C[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)O
Properties
Chemical formula	C12H15NO4
Molar mass	237.255 g·mol−1
Related compounds
Related N-acyl-alpha-amino acids	N-Acetylaspartic acid N-acetylcysteine N-Acetylglutamic acid N-Acetylglutamine N-Acetylleucine N-formylmethionine
Related compounds	Lactamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

It has also been reported that as an additive, N-L-lactoyl phenylalanine improves the taste of food, conferring an umami flavor.^[12] It is found naturally in significant amounts in some traditional Chinese fermented foods such as preserved pickles and soy sauce,^[13] and in Parmigiano-Reggiano cheese.^[14] Oral intake of Lac-Phe does not have anti-obesity effects in mice, though intraperitoneal injection does reduce food intake and weight gain.^[6] Activity dependent cell labeling indicates Lac-Phe activated neural populations in the hypothalamus and brainstem. ^[15]

See also

• Acyl group
  • Lactoyl, the acyl group derived from lactic acid
• Alpha-amino acid
• Dipeptide
• Dipeptidase